TWI292759B - Novel compound useful in the treatment of human peroxisome proliferator activate receptors (hppars) related diseases or conditions - Google Patents

Novel compound useful in the treatment of human peroxisome proliferator activate receptors (hppars) related diseases or conditions Download PDF

Info

Publication number: TWI292759B
Authority: TW; Taiwan
Prior art keywords: methyl; phenoxy; trifluoromethylphenyl; propionic acid; ethoxy
Prior art date: 2000-12-20

Application number

TW090131348A

Other languages

English (en)

Chinese (zh)

Inventor

Luc Marie Gosmini Romain

Hurst Lambert Millard Iii

Lawrence Sierra Michael

Cadilla Rodolfo

Original Assignee

Glaxo Group Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-12-20

Filing date

2001-12-18

Publication date

2008-01-21

2001-12-18 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2008-01-21 Application granted granted Critical

2008-01-21 Publication of TWI292759B publication Critical patent/TWI292759B/zh

Links

150000001875 compounds Chemical class 0.000 title claims description 178
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 19
201000010099 disease Diseases 0.000 title claims description 18
238000011282 treatment Methods 0.000 title claims description 11
239000003614 peroxisome proliferator Substances 0.000 title description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 220
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 101
235000019260 propionic acid Nutrition 0.000 claims description 59
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 52
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 38
-1 Ethyl {1-[4-methyl-2-(4-trifluoromethylphenyl)-pyrazole-5-yl]ethoxy}phenoxy Chemical group 0.000 claims description 36
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 36
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 25
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
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125000000217 alkyl group Chemical group 0.000 claims description 12
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
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125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 8
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HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 8
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ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
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238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
235000015523 tannic acid Nutrition 0.000 description 1
229940033123 tannic acid Drugs 0.000 description 1
229920002258 tannic acid Polymers 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229960005187 telmisartan Drugs 0.000 description 1
125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
125000005557 thiazolylene group Chemical group 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
238000013518 transcription Methods 0.000 description 1
230000035897 transcription Effects 0.000 description 1
230000002103 transcriptional effect Effects 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
229960001641 troglitazone Drugs 0.000 description 1
GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
238000002525 ultrasonication Methods 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
239000008215 water for injection Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/26—Radicals substituted by sulfur atoms

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Diabetes (AREA)
Obesity (AREA)
Hematology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Biomedical Technology (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Hospice & Palliative Care (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Child & Adolescent Psychology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

TW090131348A 2000-12-20 2001-12-18 Novel compound useful in the treatment of human peroxisome proliferator activate receptors (hppars) related diseases or conditions TWI292759B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB0031107.6A GB0031107D0 (en)	2000-12-20	2000-12-20	Chemical compounds

Publications (1)

Publication Number	Publication Date
TWI292759B true TWI292759B (en)	2008-01-21

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ID=9905492

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Application Number	Title	Priority Date	Filing Date
TW090131348A TWI292759B (en)	2000-12-20	2001-12-18	Novel compound useful in the treatment of human peroxisome proliferator activate receptors (hppars) related diseases or conditions

Country Status (27)

Country	Link
EP (1)	EP1343773B1 (no)
JP (1)	JP4209681B2 (no)
KR (1)	KR100815022B1 (no)
CN (1)	CN1252057C (no)
AR (1)	AR035522A1 (no)
AT (1)	ATE344253T1 (no)
AU (1)	AU2002246713B2 (no)
BR (1)	BR0116370A (no)
CA (1)	CA2432188A1 (no)
CY (1)	CY1105915T1 (no)
CZ (1)	CZ20031737A3 (no)
DE (1)	DE60124302T2 (no)
DK (1)	DK1343773T3 (no)
ES (1)	ES2274914T3 (no)
GB (1)	GB0031107D0 (no)
HU (1)	HUP0400837A3 (no)
IL (2)	IL156436A0 (no)
MX (1)	MXPA03005699A (no)
MY (1)	MY136685A (no)
NO (1)	NO20032801L (no)
NZ (1)	NZ526543A (no)
PL (1)	PL365797A1 (no)
PT (1)	PT1343773E (no)
SI (1)	SI1343773T1 (no)
TW (1)	TWI292759B (no)
WO (1)	WO2002062774A1 (no)
ZA (1)	ZA200304679B (no)

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RU2412935C2 (ru)	2005-06-30	2011-02-27	Хай Пойнт Фармасьютикалс, ЛЛС	Феноксиуксусные кислоты в качестве активаторов дельта рецепторов ppar
JO3006B1 (ar)	2005-09-14	2016-09-05	Janssen Pharmaceutica Nv	املاح ليسين مبتكرة من مشتقات حامض 4-((فينوكسي الكيل)ثيو) فينوكسي الخليك
US7582803B2 (en)	2005-09-14	2009-09-01	Amgen Inc.	Conformationally constrained 3-(4-hydroxy-phenyl)-substituted-propanoic acids useful for treating metabolic disorders
ES2386734T3 (es)	2005-12-22	2012-08-28	High Point Pharmaceuticals, Llc	Ácidos fenoxiacéticos como activadores de PPAR-DELTA
CN101007790B (zh) *	2006-01-27	2011-03-30	北京摩力克科技有限公司	草氨酸衍生物、其制备方法和医药用途
CA2645719A1 (en)	2006-03-09	2007-09-13	High Point Pharmaceuticals, Llc	Compounds that modulate ppar activity, their preparation and use
PE20080188A1 (es) *	2006-04-18	2008-03-10	Janssen Pharmaceutica Nv	Derivados del acido benzoazepin-oxi-acetico como agonistas de ppar-delta usados para aumentar hdl-c, reducir ldl-c y reducir colesterol
AU2007293028B2 (en)	2006-09-07	2012-05-31	Amgen Inc.	Heterocyclic GPR40 modulators
CA2662242C (en)	2006-09-07	2012-06-12	Amgen Inc.	Benzo-fused compounds for use in treating metabolic disorders
CA2669639A1 (en)	2006-12-02	2008-06-05	Seoul National University Industry Foundation	Aryl compounds as ppar ligands and their use
EP2104666A4 (en)	2007-01-08	2011-05-25	Seoul Nat Univ Ind Foundation	THIAZOL COMPOUND (AS PPAR DELTA LIGAND), AND PHARMACEUTICAL, COSMETIC AND HEALTHY FOOD THEREOF
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2000
- 2000-12-20 GB GBGB0031107.6A patent/GB0031107D0/en not_active Ceased
2001
- 2001-12-18 TW TW090131348A patent/TWI292759B/zh active
- 2001-12-18 AR ARP010105863A patent/AR035522A1/es not_active Application Discontinuation
- 2001-12-19 IL IL15643601A patent/IL156436A0/xx active IP Right Grant
- 2001-12-19 MY MYPI20015760A patent/MY136685A/en unknown
- 2001-12-19 KR KR1020037008392A patent/KR100815022B1/ko not_active Expired - Fee Related
- 2001-12-19 EP EP01994305A patent/EP1343773B1/en not_active Expired - Lifetime
- 2001-12-19 HU HU0400837A patent/HUP0400837A3/hu unknown
- 2001-12-19 MX MXPA03005699A patent/MXPA03005699A/es active IP Right Grant
- 2001-12-19 JP JP2002562729A patent/JP4209681B2/ja not_active Expired - Fee Related
- 2001-12-19 PL PL01365797A patent/PL365797A1/xx not_active Application Discontinuation
- 2001-12-19 CA CA002432188A patent/CA2432188A1/en not_active Abandoned
- 2001-12-19 WO PCT/US2001/049230 patent/WO2002062774A1/en not_active Ceased
- 2001-12-19 BR BR0116370-1A patent/BR0116370A/pt not_active IP Right Cessation
- 2001-12-19 NZ NZ526543A patent/NZ526543A/en unknown
- 2001-12-19 CN CNB018223095A patent/CN1252057C/zh not_active Expired - Fee Related
- 2001-12-19 CZ CZ20031737A patent/CZ20031737A3/cs unknown
- 2001-12-19 PT PT01994305T patent/PT1343773E/pt unknown
- 2001-12-19 SI SI200130672T patent/SI1343773T1/sl unknown
- 2001-12-19 ES ES01994305T patent/ES2274914T3/es not_active Expired - Lifetime
- 2001-12-19 AU AU2002246713A patent/AU2002246713B2/en not_active Ceased
- 2001-12-19 DE DE60124302T patent/DE60124302T2/de not_active Expired - Fee Related
- 2001-12-19 DK DK01994305T patent/DK1343773T3/da active
- 2001-12-19 AT AT01994305T patent/ATE344253T1/de not_active IP Right Cessation
2003
- 2003-06-12 IL IL156436A patent/IL156436A/en not_active IP Right Cessation
- 2003-06-17 ZA ZA200304679A patent/ZA200304679B/en unknown
- 2003-06-19 NO NO20032801A patent/NO20032801L/no not_active Application Discontinuation
2007
- 2007-01-10 CY CY20071100032T patent/CY1105915T1/el unknown

Also Published As

Publication number	Publication date
AU2002246713B2 (en)	2004-09-09
MXPA03005699A (es)	2003-10-06
CZ20031737A3 (cs)	2003-10-15
CY1105915T1 (el)	2011-04-06
AR035522A1 (es)	2004-06-02
HUP0400837A2 (hu)	2004-08-30
NO20032801D0 (no)	2003-06-19
PL365797A1 (en)	2005-01-10
NO20032801L (no)	2003-08-04
ES2274914T3 (es)	2007-06-01
SI1343773T1 (sl)	2007-04-30
CN1527822A (zh)	2004-09-08
HK1059925A1 (en)	2004-07-23
KR100815022B1 (ko)	2008-03-18
NZ526543A (en)	2004-11-26
DE60124302D1 (de)	2006-12-14
DE60124302T2 (de)	2007-05-03
HUP0400837A3 (en)	2007-11-28
JP4209681B2 (ja)	2009-01-14
ATE344253T1 (de)	2006-11-15
DK1343773T3 (da)	2007-02-05
JP2004518702A (ja)	2004-06-24
EP1343773B1 (en)	2006-11-02
GB0031107D0 (en)	2001-01-31
CN1252057C (zh)	2006-04-19
IL156436A (en)	2008-06-05
PT1343773E (pt)	2007-02-28
ZA200304679B (en)	2004-10-04
MY136685A (en)	2008-11-28
KR20030072571A (ko)	2003-09-15
WO2002062774A1 (en)	2002-08-15
EP1343773A1 (en)	2003-09-17
CA2432188A1 (en)	2002-08-15
BR0116370A (pt)	2003-12-09
IL156436A0 (en)	2004-01-04

Publication	Publication Date	Title
TWI292759B (en)	2008-01-21	Novel compound useful in the treatment of human peroxisome proliferator activate receptors (hppars) related diseases or conditions
KR100668026B1 (ko)	2007-02-28	티아졸 및 옥사졸 유도체 및 그의 제약적 용도
AU2002246713A1 (en)	2003-02-13	Thiazole derivatives for treating PPAR related disorders
CA2339773A1 (en)	2000-02-17	Substituted oxazoles and thiazoles derivatives as hppar gamma and hppar alpha activators
JP2004532266A (ja)	2004-10-21	心血管系疾患の治療に有用なチアゾールまたはオキサゾール誘導体
KR20070057230A (ko)	2007-06-04	헥사플루오로아이소프로판올 치환된 에터 유도체
JP2005529965A (ja)	2005-10-06	ｈＰＰＡＲ活性化物質としてのフェニルオキシアルカン酸誘導体
JP2004517100A (ja)	2004-06-10	ｈＰＰＡＲアルファアゴニストとしての置換オキサゾールおよびチアゾール
AU2006311675A1 (en)	2007-05-18	Compounds and compositions as PPAR modulators
KR100859591B1 (ko)	2008-09-23	Ｈｐｐａｒ-알파 수용체의 옥사졸/티아졸-유도체 활성제
US20040132787A1 (en)	2004-07-08	1, 2, 4-Oxadiazole derivatives as hppar alpha agonists
US7105551B2 (en)	2006-09-12	Thiazole derivatives for treating PPAR related disorders
HK1059925B (en)	2007-06-15	Thiazole derivatives for treating ppar related disorders